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Cheap flights from Chicago Midway Airport to Milan from $298

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 3/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
KLM Logo
1:05 pm - 9:25 am
MDW
-
MXP
13h 20m
1 stop
KLM Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
$901KLM
Sun, Aug 16 - Mon, Aug 31
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
9:45 am - 7:46 am
MXP
-
MDW
29h 01m
2 stops
$941Multiple Airlines
Thu, Apr 16 - Sun, May 3
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
12:55 pm - 9:40 am
MXP
-
MDW
27h 45m
2 stops
$987Multiple Airlines
Thu, May 14 - Wed, May 20
Multiple Airlines Logo
9:25 am - 3:50 pm
MDW
-
MXP
23h 25m
2 stops
Multiple Airlines Logo
6:55 am - 8:45 pm
MXP
-
MDW
20h 50m
2 stops
$993Multiple Airlines
Mon, May 18 - Thu, May 28
Delta Logo
12:52 pm - 12:05 pm
MDW
-
MXP
16h 13m
2 stops
Delta Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$1,001Delta
Wed, Apr 22 - Wed, Apr 29
Delta Logo
1:24 pm - 11:20 am
MDW
-
LIN
14h 56m
2 stops
Delta Logo
6:40 am - 4:26 pm
LIN
-
MDW
16h 46m
2 stops
$1,008Delta
Mon, Apr 20 - Tue, May 5
Delta Logo
1:24 pm - 2:45 pm
MDW
-
MXP
18h 21m
2 stops
Delta Logo
6:45 am - 6:36 pm
MXP
-
MDW
18h 51m
2 stops
$1,012Delta
Mon, Apr 20 - Thu, Apr 30
Multiple Airlines Logo
9:00 am - 3:50 pm
MDW
-
MXP
23h 50m
2 stops
Multiple Airlines Logo
7:00 am - 7:20 pm
MXP
-
MDW
19h 20m
2 stops
$1,028Multiple Airlines
Tue, Jun 9 - Tue, Jun 16
Delta Logo
10:41 am - 12:05 pm
MDW
-
MXP
18h 24m
2 stops
Delta Logo
9:00 am - 10:28 pm
MXP
-
MDW
20h 28m
2 stops
$1,051Delta
Sat, Apr 18 - Wed, Apr 29
Multiple Airlines Logo
1:24 pm - 11:20 am
MDW
-
LIN
14h 56m
2 stops
Multiple Airlines Logo
6:40 am - 4:26 pm
LIN
-
MDW
16h 46m
2 stops
$1,051Multiple Airlines
Mon, Apr 20 - Tue, May 5

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets
Delta
Apr 22
MDW12:52 pmChicago Midway
16h 13m
2 stops
MXP12:05 pmMilan Malpensa
Apr 29
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$1,001
Delta
Apr 20
MDW1:24 pmChicago Midway
14h 56m
2 stops
LIN11:20 amMilan Linate
May 5
LIN6:40 amMilan Linate
16h 46m
2 stops
MDW4:26 pmChicago Midway
$1,008
Delta
Apr 20
MDW1:24 pmChicago Midway
18h 21m
2 stops
MXP2:45 pmMilan Malpensa
Apr 30
MXP6:45 amMilan Malpensa
18h 51m
2 stops
MDW6:36 pmChicago Midway
$1,012

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets
KLM
Aug 16
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 31
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$901
KLM
Apr 15
MDW10:41 amChicago Midway
15h 44m
1 stop
MXP9:25 amMilan Malpensa
Apr 22
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$1,094
KLM
Jul 27
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$1,121

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Milan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 8/16

1:05 pm-9:25 am

1 stop13h 20m

Milan Malpensa

Mon 8/31

11:40 am-9:46 pm

1 stop17h 06m

$901

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 4/16

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Sun 5/3

9:45 am-7:46 am

2 stops29h 01m

$941

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 5/14

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Wed 5/20

12:55 pm-9:40 am

2 stops27h 45m

$987

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 5/18

9:25 am-3:50 pm

2 stops23h 25m

Milan Malpensa

Thu 5/28

6:55 am-8:45 pm

2 stops20h 50m

$993

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 4/22

12:52 pm-12:05 pm

2 stops16h 13m

Milan Malpensa

Wed 4/29

11:40 am-10:28 pm

1 stop17h 48m

$1,001

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 4/20

1:24 pm-11:20 am

2 stops14h 56m

Milan Linate

Tue 5/5

6:40 am-4:26 pm

2 stops16h 46m

$1,008

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 4/20

1:24 pm-2:45 pm

2 stops18h 21m

Milan Malpensa

Thu 4/30

6:45 am-6:36 pm

2 stops18h 51m

$1,012

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 6/9

9:00 am-3:50 pm

2 stops23h 50m

Milan Malpensa

Tue 6/16

7:00 am-7:20 pm

2 stops19h 20m

$1,028

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 4/18

10:41 am-12:05 pm

2 stops18h 24m

Milan Malpensa

Wed 4/29

9:00 am-10:28 pm

2 stops20h 28m

$1,051

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 4/20

1:24 pm-11:20 am

2 stops14h 56m

Milan Linate

Tue 5/5

6:40 am-4:26 pm

2 stops16h 46m

$1,051

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,184. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,366.

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

12h 56m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan takes 12h 56m
There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.
Search flight deals

  • How far is Chicago Midway to Milan by plane?

    Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 12h 56m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Milan?

    Prices for flights from Chicago Midway Airport to Milan are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Milan?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

  • What documentation or ID do you need to fly to Milan?

    The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Menaggio
Brescia
Stresa
Livigno
Levanto
Monza
Assago
Bellano
Lecco
Crema
Domodossola
Rho
Cernobbio
Moltrasio
Saronno
Bormio
Baveno
Novara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport